The Milwaukee Bucks are about to enter possibly the most pivotal season of their franchise's history. They've been graced with the fortune of drafting Giannis Antetokounmpo years ago after he slipped to them with the 15th pick, and that for the most part has returned some success in watching him develop into a two-time MVP.

Still, Antetokounmpo's time with Milwaukee isn't guaranteed, and the Bucks front office is well aware of that. In today's era of loyalty, Antetokounmpo's faithfulness to Milwaukee ranks at the top of the list. He's long stated his desire to remain with the Bucks for his entire career, but as a top-tier talent, he also craves the possibility of playing at the highest level, which hasn't happened yet.

The Bucks knew coming into this offseason that each move that was made, despite how miniscule it may be, would aid in the pending decision of Antetokounmpo electing to sign his max extension by Dec.21.

They were able to make some significant moves that'll still be on a wait-and-see basis once the season begins, and how their actual offseason success will rank depends on Antetokounmpo's decision coming into the season.

Offseason Grade: B-

Draft: 

The Bucks were set with their No. 24 pick in the draft, which ended up being guard sensation R.J. Hampton. Unfortunately, Hampton was shipped off to Denver as part of a the Jrue-Holiday deal. Hampton would've been a young, raw talent at the guard position for the Bucks, but it makes sense that Milwaukee didn't want to invest so much into the 19-year old with the focus of Antetokounmpo on the forefront of everything.

They were able to draft Jordan Nwora with the 45th pick, but his time with the squad may be limited for his first season. The Bucks are solidified on forwards at the moment, which may offer little opportunity to the 22-year old.

Trades: 

Milwaukee made a major upgrade at the point guard position after landing Holiday in exchange for Eric Bledsoe, George Hill, three first-round picks along with a couple of draft swap rights. The bulk of work it took to acquire Holiday may make them losers of the deal in years to come, but the front office is in win-now mode and can't harp on that in the moment.

Holiday is one of the more solid defenders in the league as was Bledsoe, but he also brings a more efficient game on offense. If Holiday is able to blend into the Bucks' system seamlessly, they could possibly lift themselves once more to the top of the Eastern Conference.

Where the Bucks did take a loss in the trade department was with the failed acquisition of Bogdan Bogdanovic. The 28-year old was a high target on the Bucks' radar seeing as how Antetokounmpo had tried to recruit the sharpshooter to Milwaukee this offseason. The mismanagement on behalf of the Bucks front office could end up altering Antetokounmpo's decision in staying long term. If not for them dropping the ball, the Bucks would have one of the more scarier starting lineups in the league.

Free Agency:

This free agency market was already set to be one of the weaker ones in recent memory given the ongoing pandemic and shortened window between last season and the upcoming one. Still, the Bucks were able to attract some decent role players to their roster that should help fill in some voids left by exiting players.

Bobby Portis, who signed a two-year, $ 7.4 million deal, can bring immediate intensity in the frontcourt for the Bucks when Antetokounmpo takes a seat on the bench. Portis is still young at the age of 25 and could turn his career around in Milwaukee.

After becoming a centerpiece with the Chicago Bulls for four seasons, Portis bounced around the league before signing with the Bucks. He averaged 10.1 points, 5.1 rebounds and 1.5 assists last season with the New York Knicks.

Another huge pickup for the Bucks was DJ Augustin. Augustin was a popular name in the free agency pool this offseason with many contenders being in need of either a starting or high-caliber backup point guard. He can contribute immediately to a Bucks offense that lost a bit of 3-point shooting this offseason. There's a strong possibility that he could start alongside Holiday in the backcourt, which could prove to be beneficial.

Torrey Craig was a player that went under the radar before signing with the Bucks. His playing time and production diminished with the Denver Nuggets, but he's still a capable scorer and defender off the bench.

Outlook: 

From a talent aspect, the Bucks didn't move the needle in getting better. The bulk of their success will depend on Holiday forming into a Big 3 alongside Antetokounmpo and Khris Middleton. Aside from that, most of the additions are replacements that balance out the talent level they boasted last season.

There will be a lot of teams making their claim for the top spot in the Eastern Conference this season, primarily the Brooklyn Nets. If the Bucks are to have any success, it'll start with immediately forming chemistry and capitalizing on it.